Antiproliferative activity of the Michael adducts of aroylacrylic acids and cyclic amines
Antiproliferative activity of twenty one Michael adducts of aroylacrylic acids and cyclic amines ( N -Me-piperazine, imidazole, 2-Me-imidazole, and indole) was tested toward five human tumor cell lines (HeLa, LS174, K562, FemX, MDA-MB-361) in vitro. Compounds exerted antiproliferative activity in th...
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| Published in: | Molecular diversity Vol. 18; no. 3; pp. 577 - 592 |
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| Abstract | Antiproliferative activity of twenty one Michael adducts of aroylacrylic acids and cyclic amines (
N
-Me-piperazine, imidazole, 2-Me-imidazole, and indole) was tested toward five human tumor cell lines (HeLa, LS174, K562, FemX, MDA-MB-361) in vitro. Compounds exerted antiproliferative activity in the high to the single-digit micromolar concentrations, causing increase of the cell population fraction in S phase and apoptosis.
N
-Me-piperazine and imidazole derivatives of aroylacrylic acids substituted with bulky alkyl substituents (2,4-di-
i
-Pr-Ph-, 2,4,6-tri-Et-Ph-, or
β
-tetrahydronaphthyl-) showed the best potency, while indole adducts were proved as the inferior antiproliferative agents. Few compounds showed significant selectivity, tumor versus healthy cells, with selectivity index
∼
60
for the most selective congener. An unbiased in silico distinction between more and less potent compounds was obtained from 3D QSAR models derived by alignment-independent GRIND-2 descriptors.
Graphical Abstract |
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| AbstractList | (ProQuest: ... denotes formulae and/or non-USASCII text omitted; see image) Antiproliferative activity of twenty one Michael adducts of aroylacrylic acids and cyclic amines (...-Me-piperazine, imidazole, 2-Me-imidazole, and indole) was tested toward five human tumor cell lines (HeLa, LS174, K562, FemX, MDA-MB-361) in vitro. Compounds exerted antiproliferative activity in the high to the single-digit micromolar concentrations, causing increase of the cell population fraction in S phase and apoptosis. ...-Me-piperazine and imidazole derivatives of aroylacrylic acids substituted with bulky alkyl substituents (2,4-di-...-Pr-Ph-, 2,4,6-tri-Et-Ph-, or ...-tetrahydronaphthyl-) showed the best potency, while indole adducts were proved as the inferior antiproliferative agents. Few compounds showed significant selectivity, tumor versus healthy cells, with selectivity index ... for the most selective congener. An unbiased in silico distinction between more and less potent compounds was obtained from 3D QSAR models derived by alignment-independent GRIND-2 descriptors. [Figure not available: see fulltext.][PUBLICATION ABSTRACT] Antiproliferative activity of twenty one Michael adducts of aroylacrylic acids and cyclic amines ( N -Me-piperazine, imidazole, 2-Me-imidazole, and indole) was tested toward five human tumor cell lines (HeLa, LS174, K562, FemX, MDA-MB-361) in vitro. Compounds exerted antiproliferative activity in the high to the single-digit micromolar concentrations, causing increase of the cell population fraction in S phase and apoptosis. N -Me-piperazine and imidazole derivatives of aroylacrylic acids substituted with bulky alkyl substituents (2,4-di- i -Pr-Ph-, 2,4,6-tri-Et-Ph-, or β -tetrahydronaphthyl-) showed the best potency, while indole adducts were proved as the inferior antiproliferative agents. Few compounds showed significant selectivity, tumor versus healthy cells, with selectivity index ∼ 60 for the most selective congener. An unbiased in silico distinction between more and less potent compounds was obtained from 3D QSAR models derived by alignment-independent GRIND-2 descriptors. Graphical Abstract Antiproliferative activity of twenty one Michael adducts of aroylacrylic acids and cyclic amines (N-Me-piperazine, imidazole, 2-Me-imidazole, and indole) was tested toward five human tumor cell lines (HeLa, LS174, K562, FemX, MDA-MB-361) in vitro. Compounds exerted antiproliferative activity in the high to the single-digit micromolar concentrations, causing increase of the cell population fraction in S phase and apoptosis. N-Me-piperazine and imidazole derivatives of aroylacrylic acids substituted with bulky alkyl substituents (2,4-di-i-Pr-Ph-, 2,4,6-tri-Et-Ph-, or β-tetrahydronaphthyl-) showed the best potency, while indole adducts were proved as the inferior antiproliferative agents. Few compounds showed significant selectivity, tumor versus healthy cells, with selectivity index ~60 for the most selective congener. An unbiased in silico distinction between more and less potent compounds was obtained from 3D QSAR models derived by alignment-independent GRIND-2 descriptors. |
| Author | Tošić, Ana V. Juranić, Ivan O. Kolundžija, Branka Drakulić, Branko J. |
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| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/24874228$$D View this record in MEDLINE/PubMed |
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| CitedBy_id | crossref_primary_10_31857_S0132344X23600182 crossref_primary_10_1134_S1070328423600584 crossref_primary_10_3389_fmicb_2017_01767 crossref_primary_10_1002_jhet_2375 |
| Cites_doi | 10.1007/BF00119860 10.1093/nar/gkr1132 10.1021/ja01190a041 10.1021/ci300314k 10.1002/(SICI)1096-987X(199905)20:7<730::AID-JCC8>3.0.CO;2-T 10.3390/12010025 10.1021/jm00145a002 10.1021/ci800037t 10.1016/0022-1759(83)90303-4 10.1021/ml200141e 10.1021/cb200404c 10.1021/jm0502889 10.1016/j.ejmech.2013.01.006 10.1016/j.ejmech.2011.04.043 10.1016/0022-1759(91)90327-C 10.1023/B:JCAM.0000035186.90683.f2 10.1021/ja01598a058 10.1021/ci100031x |
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| DOI | 10.1007/s11030-014-9528-4 |
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| Keywords | Michael adducts 3D QSAR Selectivity Antiproliferative activity Aroylacrylic acids |
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N
-Me-piperazine, imidazole, 2-Me-imidazole, and indole) was... Antiproliferative activity of twenty one Michael adducts of aroylacrylic acids and cyclic amines (N-Me-piperazine, imidazole, 2-Me-imidazole, and indole) was... (ProQuest: ... denotes formulae and/or non-USASCII text omitted; see image) Antiproliferative activity of twenty one Michael adducts of aroylacrylic acids and... |
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| SubjectTerms | Acids Acrylates - chemistry Acrylates - pharmacology Amines - chemistry Amines - pharmacology Antineoplastic Agents - chemistry Antineoplastic Agents - pharmacology Biochemistry Biomedical and Life Sciences Cell Line, Tumor Cell Proliferation - drug effects Chemical engineering Full-Length Paper Humans Life Sciences Models, Molecular Molecular chemistry Molecular Conformation Organic Chemistry Pharmacy Polymer Sciences |
| Title | Antiproliferative activity of the Michael adducts of aroylacrylic acids and cyclic amines |
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